AVM Osley joined the Air Force in January 1977. He flew as an Air Combat Officer in F-111 strike aircraft with No 1 Squadron before being posted on exchange to fly in reconnaissance Phantoms with the USAF in Texas. On return to Australia in 1988, he flew reconnaissance RF-111C aircraft with No 6 Squadron.
In the period 1990-93, AVM Osley was responsible for major strike-reconnaissance projects within Capability Development (Air) Branch. Following staff training in 1994, he was the Air Force strategic planner for three years before taking command of No 1 Squadron (F-111).
On promotion to Group Captain in late 1999, AVM Osley was posted to the United Kingdom as the Air Force Adviser. In 2002 he undertook senior staff studies before being appointed Officer Commanding No 82 Wing. In August 2004 he was posted on promotion to Director General Capability and Plans, Canberra. In this position he assisted with planning the future force structure for the Australian Defence Force.
AVM Osley deployed as Director of the Combined Air Operations Centre in the Middle East in the period November 2006 to March 2007. In this position, he directed all Coalition air operations over Iraq and Afghanistan. He took up the appointment of Commander Air Combat Group in July 2007. Following studies at Harvard Business School in early 2008, AVM Osley was promoted to his current rank and appointed as Head of Australian Defence Staff (Washington) in July 2008. In December 2010, AVM Osley returned to Australia to take up the position of Program Manager New Air Combat Capability (PM NACC). In December 2013 he was posted to Air Force Headquarters as Head Capability Transition – Air Force; where he coordinated the planning for the transition of the F-35 and other Air Force capabilities into RAAF service. He retired from the Permanent Air Force on 31 August 2014.
In addition to full-time employment as a Director in Pricewaterhouse Coopers, AVM Osley continues to support RAAF senior international engagement activities in uniform and recently conducted a review into leadership and ethics education. He is also the Patron of the Australian Federation Guard, Patron of the 467/463 Squadrons (Qld) Association, Vice President of the WW2 Pathfinders (Qld) Association, and Executive Secretary and Fellow of the Australian Institute of Navigation.
AVM Osley has a BSc (Physics), Master of Arts, Master of Def Stud, Grad Dip Mngt, Grad Dip Mil Av, is a Fellow of the Centre for Defence and Strategic Studies, is a graduate of the Harvard Business School (Advanced Management Program) and a Graduate of the Australian Institute of Company Directors. He is married to Debbie, has three grown children, and his interests include writing military biographies, history, classic car restoration, road cycling, and travel. He was awarded a Conspicuous Service Cross for Services to Air Force in 1997, and made a Member of the Order of Australia in 2008.